Fluorous organocatalysis

Topics in Current Chemistry

Volumn 308, Issue , 2012, Pages 175-190

  Zhang, Wei ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

Asymmetric synthesis; Fluorous; Green chemistry; Organocatalysis

Indexed keywords

AMINE; CINCHONA ALKALOID; FLUOROCARBON; THIOUREA;

ARTICLE; CATALYSIS; CHEMISTRY;

AMINES; CATALYSIS; CINCHONA ALKALOIDS; FLUOROCARBONS; THIOUREA;

EID: 81855166712     PISSN: 03401022     EISSN: None     Source Type: Book Series    
DOI: 10.1007/128_2011_257     Document Type: Article

References (44)

1. Berkessel A, Groger H (2005) Asymmetric organocatalysis. Wiley-VCH, Weinheim
2. Dalko PI (2007) Enantioselective organocatalysis. Wiley-VCH, Weinheim
3. Anastas PT, Warner JC (1998) Green chemistry: theory and practice. Oxford University Press, Oxford
4. Cozzi F (2006) Immobilization of organic catalysts: when, why, and how. Adv Synth Catal 348:1367
5. de Maria PD (2008) "Nonsolvent" applications of ionic liquids in biotransformations and organocatalysis. Angew Chem Int Ed Engl 47:6960
6. Zhang W, Cai C (2008) New chemical and biological applications of fluorous technologies. Chem Commun 44:5686
7. Horvath IT (1998) Fluorous biphase chemistry. Acc Chem Res 31:641
8. de Wolf E, van Koten G, Deelman BJ (1999) Fluorous phase separation techniques in catalysis. Chem Soc Rev 28:37
9. Barthel-Rosa LP, Gladysz JA (1999) Chemistry in fluorous media: a user's guide to practical considerations in the application of fluorous catalysts and reagents. Coord Chem Rev 190-192:587
10. Pozzi G, Shepperson I (2003) Fluorous chiral ligands for novel catalytic systems. Coord Chem Rev 242:115
11. Zhang W, Curran DP (2006) Synthetic applications of fluorous solid-phase extraction (F-SPE). Tetrahedron 62:11837
12. Nakamura Y, Takeuchi S, Okumura K, Ohgo Y (2001) Enantioselective addition of diethylzinc to aldehydes catalyzed by fluorous beta-aminoalcohols. Tetrahedron 57:5565
13. Fache F, Piva O (2001) New perfluoroalkylated cinchona derivatives: synthesis and use in base-catalysed Diels-Alder reactions. Tetrahedron Lett 42:5655
14. Ishihara K, Kondo S, Yamamoto H (2001) 3,5-Bis(perfluorodecyl) phenylboronic acid as an easily recyclable direct amide condensation catalyst. Synlett 1371
15. Zhang Z, Zhang W (2011) Fluorous organocatalysis-a green approach for asymmetric synthesis. Chim Oggi 28(3):32
16. Cai C, Yi WB, Zhang W, Shen MG, Hong M, Zeng LY (2009) Fluorous Lewis acids and phase transfer catalysts. Mol Divers 13:209
17. Notz W, Tanaka F, Barbas CF (2004) Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-Alder reactions. Acc Chem Res 37:80
18. Zu LS, Wang J, Li H, Wang W (2006) A recyclable fluorous (S)-pyrrolidine sulfonamide promoted direct, highly enantioselective Michael addition of ketones and aldehydes to nitroolefins in water. Org Lett 8:3077
19. Zu LS, Xie HX, Li H, Wang J, Wang W (2008) Highly enantioselective aldol reactions catalyzed by a recyclable fluorous (S) pyrrolidine sulfonamide on water. Org Lett 10:1211
20. Fache F, Piva O (2003) Synthesis and applications of the first polyfluorous proline derivative. Tetrahedron Asymmetry 14:139
21. Chu QL, Zhang W, Curran DP (2006) A recyclable fluorous organocatalyst for Diels-Alder reactions. Tetrahedron Lett 47:9287
22. Malkov AV, Figlus M, Stoncius S, Kocovsky P (2007) Organocatalysis with a fluorous tag: asymmetric reduction of imines with trichlorosilane catalyzed by amino acid-derived formamides. J Org Chem 72:1315
23. Park JK, Lee HG, Bolm C, Kim BM (2005) Asymmetric diethyl-and diphenylzinc additions to aldehydes by using a fluorine-containing chiral amino alcohol: a striking temperature effect on the enantioselectivity, a minimal amino alcohol loading, and an efficient recycling of the amino alcohol. Chem Eur J 11:945
24. Dalicsek Z, Pollreisz F, Gomory A, Soos T (2005) Recoverable fluorous CBS methodology for asymmetric reduction of ketones. Org Lett 7:3243
25. Chu QL, Yu MS, Curran DP (2008) CBS reductions with a fluorous prolinol immobilized in a hydrofluoroether solvent. Org Lett 10:749
26. Dalicsek Z, Pollreisz F, Soos T (2009) Efficient separation of a trifluoromethyl substituted organocatalyst: just add water. Chem Commun 4587
27. Goushi S, Funabiki K, Ohta M, Hatano K, Matsui M (2007) Novel fluorous prolinol as a precatalyst for catalytic asymmetric borane reduction of various ketones. Tetrhedron 63:4061
28. Zu LS, Li H, Wang J, Yu XH, Wang W (2006) Highly enantioselective aldehyde-nitroolefin Michael addition reactions catalyzed by recyclable fluorous (S) diphenylpyrrolinol silyl ether. Tetrahedron Lett 47:5131
29. Cui HF, Li YW, Zheng CW, Zhao G, Zhu SS (2008) Enantioselective catalytic epoxidation of alpha, beta-enones promoted by fluorous alpha, alpha-diaryl-L-prolinols. J Fluor Chem 129:45
30. Song CE (2009) Cinchona alkaloids in synthesis and catalysis. Wiley-VCH, Weinheim
31. Tian SK, Chen YG, Hang JF, Tang L, McDaid P, Deng L (2004) Asymmetric organic catalysis with modified cinchona alkaloids. Acc Chem Res 37:621
32. Xu XH, Kusuda A, Tokunaga E, Shibata N (2011) Catalyst-free and catalytic Friedel-Crafts alkylations of indoles in Solkane (R) 365mfc, an environmentally benign alternative solvent. Green Chem 13:46
33. Zhang ZG, Schreiner PR (2009) (Thio)urea organocatalysis-what can be learnt from anion recognition? Chem Soc Rev 38:1187
34. Huang YB, Yi WB, Cai C (2010) An efficient, recoverable fluorous organocatalyst for direct reductive amination of aldehydes. J Fluor Chem 132:879
35. Wang L, Cai C, Curran DP, ZhangW(2010) Enantioselective alpha-chlorination of aldehydes with recyclable fluorous (S)-pyrrolidine- thiourea bifunctional organocatalyst. Synlett 433
36. Miura T, Itoh K, Yasaku Y, Koyata N, Murakami Y, Imai N (2008) Catalytic enantioselective cyclopropanation of allylic alcohols using recyclable fluorous disulfonamide ligand. Tetrahedron Lett 49:5813
37. Miura T, Imai K, Ina M, Tada N, Imai N, Itoh A (2010) Direct asymmetric aldol reaction with recyclable fluorous organocatalyst. Org Lett 12:1620
38. Miura T, Nakashima K, Tada N, Itoh A (2011) An effective and catalytic oxidation using recyclable fluorous IBX. Chem Commun 47:1875
39. Legros J, Crousse B, Bonnet-Delpon D (2008) Fluorous analogues of DMAP (F-DMAP): reusable organocatalysts for acylation reaction. J Fluor Chem 129:974
40. Vuluga D, Legros J, Crousse B, Bonnet-Delpon D (2010) Fluorous 4-N,N-dimethylaminopyridine (DMAP) salts as simple recyclable acylation catalysts. Chem Eur J 16:1776
41. Gimbert C, Vallribera A, Gladysz JA, Jurisch M (2010) Thermomorphic fluorous phosphines as organocatalysts for Michael addition reactions. Tetrahedron Lett 51:4662
42. Seidel FO, Gladysz JA (2008) Catalysis of intramolecular Morita-Baylis-Hiliman and Rauhut-Currier reactions by fluorous phosphines; facile recovery by liquid/solid organic/fluorous biphase protocols involving precipitation, Teflon (R) tape, and Gore-Rastex (R) fiber. Adv Synth Catal 350:2443
43. Bruckmann A, Pena MA, Bolm C (2008) Organocatalysis through halogen-bond activation. Synlett 900
44. Dordonne S, Crousse B, Bonnet-Depon D, Legros J (2011) Fluorous tagging of DABCO through halogen bonding: recyclable catalyst for the Morita-Baylis-Hillman reaction. Chem Commun 47:5855